Thiourea catalyzed aminolysis of epoxides under solvent free conditions. Electronic control of regioselective ring opening

Tetrahedron

Volumn 66, Issue 16, 2010, Pages 3042-3049

  Chimni, Swapandeep Singh ^a   Bala, Neeraj ^a   Dixit, Vaibhav A ^b   Bharatam, Prasad V ^b  

^a GURU NANAK DEV UNIVERSITY   (India)

^b NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; SOLVENT; THIOUREA;

AMINOLYSIS; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; HYDROGEN BOND; PRIORITY JOURNAL; RING OPENING; STEREOCHEMISTRY;

EID: 77949773549     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.02.053     Document Type: Article

References (42)

1. Connon S.J. Synlett (2009) 354-376
2. Dondoni A., and Massi A. Angew. Chem., Int. Ed. 47 (2008) 4638-4660
3. Yu X., and Wang W. Chem. Asian. J. 3 (2008) 516-532
4. Connon S.J. Chem.-Eur. J. 12 (2006) 5418-5427
5. Wittkopp A., and Schreiner P.R. Chem.-Eur. J. 9 (2003) 407-414
6. Rink R., Kingma J., Spelberg J.H.L., and Janssen D.B. Biochemistry 39 (2000) 5600-5613
7. Curran D.P., and Kuo L.H. J. Org. Chem. 59 (1994) 3259-3261
8. Curran D.P., and Kuo L.H. Tetrahedron Lett. 36 (1995) 6647-6650
9. Sigman M.S., and Jacobsen E.N. J. Am. Chem. Soc. 120 (1998) 4901-4902
10. Schreiner P.R., and Wittkopp A. Org. Lett. 4 (2002) 217-220
11. Kleiner C.M., and Schreiner P.R. Chem. Commun. (2006) 4315-4317
12. Bonollo S., Fringuelli F., Pizzo F., and Vaccaro L. Green Chem. 8 (2006) 960-964
13. Weil T., Kotke M., Kleiner M., and Schreiner P.R. Org. Lett. 10 (2008) 1513-1516
14. Azizi N., and Saidi M.R. Org. Lett. 7 (2005) 3649-3651
15. Fleming E.M., Quigley C., Rozas I., and Connon S.J. J. Org. Chem. 73 (2008) 948-956
16. Alikhani V., Beer D., Bentley D., Bruce I., Cuenoud B.M., Fairhurst R.A., Gedeck P., Haberthuer S., Hayden C., Janus D., Jordan L., Lewis C., Smithies K., and Wissler E. Bioorg. Med. Chem. Lett. 14 (2004) 4705-4710
17. Ruediger E., Martel A., Meanwell N., Solomon C., and Turmel B. Tetrahedron Lett. 45 (2004) 739-742
18. Zhu S., Meng L., Zhang Q., and Wei L. Bioorg. Med. Chem. Lett. 16 (2006) 1854-1858
19. Yamaguchi T., Harada N., Ozaki K., and Hashiyama T. Tetrahedron Lett. 39 (1998) 5575-5578
20. Moore W.J., and Luzzio F.A. Tetrahedron Lett. 36 (1995) 6599-6602
21. Lindsay K.B., and Pyne S.G. Tetrahedron 60 (2004) 4173-4176
22. Mori K., Sakakibara M., and Okada K. Tetrahedron 40 (1984) 1767-1781
23. O'Brien P. Angew. Chem., Int. Ed. 38 (1999) 326-329
24. Li G., Chang H.-T., and Sharpless K.B. Angew. Chem., Int. Ed. 35 (1996) 451-454
25. Ager D.J., Prakash I., and Schaad D.R. Chem. Rev. 96 (1996) 835-876
26. Bordwell F.G., Algrim D.J., and Harrelson J.A. J. Am. Chem. Soc. 110 (1988) 5903-5904
27. α of styrene epoxide. Chini M., Crotti P., and Macchia F. J. Org. Chem. 56 (1991) 5939-5942
28. TON, turnover number (number of substrate molecules converted to product per catalyst molecule), i.e, conversion/catalyst mol %. TOF, turnover frequency=TON per unit hour.
29. Kayser M.M., and Morand P. Can. J. Chem. 58 (1980) 302-306
30. Mitsuru S., Tomoyuki S., and Kozo S. Tetrahedron Lett. 45 (2004) 9265-9268
31. Reines S.A., Griffith J.R., and Orear J.G. J. Org. Chem. 36 (1970) 2772-2777
32. Carlier P.R., Deora N., and Crawford T.D. J. Org. Chem. 71 (2006) 1592-1597
33. Zhao Y., and Truhlar D.G. J. Org. Chem. 72 (2007) 295-298
34. Shivani, Pujala B., and Chakraborti A.K. J. Org. Chem. 72 (2007) 3713-3722
35. Maheswara M., Rao K.S.V.K., and Do J.Y. Tetrahedron Lett. 49 (2008) 1795-1800
36. Reddy L.R., Reddy M.A., Bhanumathi N., and Rao K.R. New J. Chem. 25 (2001) 221-222
37. Placzek A.T., Donelson J.L., Trivedi R., Gibbs R.A., and De S.K. Tetrahedron Lett. 46 (2005) 9029-9034
38. Ollevier T.N.E. Tetrahedron Lett. 49 (2008) 1546-1550
39. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision E.01 (2004), Gaussian, Inc., Wallingford CT
40. Scott A.P., and Radom L. J. Phys. Chem. 100 (1996) 16502-16513
41. Reed A.E., Curtiss L.A., and Weinhold F. Chem. Rev. 88 (2002) 899-926
42. Reed A.E., Weinstock R.B., and Weinhold F. J. Chem. Phys. 83 (1985) 735-746